“I’ll never retire!”

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“I’ll never retire. It’s not worth it!”

They’re so cute when they say that.

Instead of writing yet another post about how or when to retire, I thought I’d take the devil’s-advocate approach and share the thoughts of people who aren’t sure whether any of us should ever retire. Admittedly these people are still working, they may not have actually ever experienced a true retirement, and they have not yet have had to be responsible for their own entertainment. While you could suspect their credibility, you’d be wise to avoid shooting these messengers for long enough to assess their concerns on their own merits.

First up is Robert Brokamp. He’s a CFP with some serious retirement writing chops from advising The Motley Fool’s “Rule Your Retirement” newsletter. He regularly contributes articles to Get Rich Slowly, one of the Web’s biggest personal-finance blogs. He’s also interviewed Billy & Akaisha Kaderli, who retired early over two decades ago (in their 30s) to travel the world. If anybody knows about retirement (without actually being retired), it’s Mr. Brokamp.

Yet he thinks that retirement is too risky. Here’s his list of retirement flaws, with full explanations at the link:

Social Security has “issues.”

Fewer people have pensions, and pensions have their own problems.

Savings to the rescue…or not.

Or maybe my home equity will save me…oh, wait.

Health care is unpredictable and expensive.

We might last longer than our assets.

He concludes with the thought: By the time I’m 72, I may have changed my mind — or my body has changed it for me — and I’ll actually be ready to sit on my butt all day.

Another article from White Coat Investor lists 14 reasons against retiring early. The author is a real no-foolin’ doctor and frequent poster at Bogleheads.org, whose members know quite a bit about saving for retirement. Here’s the summary of his list:

You have to sacrifice to save an uncomfortably high percentage of your income.

You have to bridge Social Security income until you’re old enough.

You have to bridge the health insurance gap until you’re old enough for Medicare.

Immediate annuities don’t pay enough in your 50s.

Early retirees don’t benefit from catch-up contributions to tax-deferred savings.

It’s cumbersome to access money from retirement accounts before age 59½.

You have less time to pay off educational debt.

You have less time to pay off the mortgage.

Paying for college for the kids becomes a much more difficult challenge.

Early retirees live longer but not as comfortably due to having less savings.

You’ll have to save expenses by doing your own investing.

You might be forced into lifestyle decisions like fewer kids or a high-pressure career.

You may identify with work too closely to be comfortable with leaving it.

Other articles from highly respected authors point out that the Boomer Generation has redefined our culture as finding work you love and doing it for the rest of your life. The Rolling Stones and the Beach Boys haven’t retired… why should the rest of us? If we can be productive, then why not get paid for it?

There are even the usual dire warnings from the “work until you drop” crowd that the Boomer generation will never have the social contract or the safety net to support our retirement.

Whew. Maybe I’ve overstated the case. I understand if you need to take a moment here to reflect on your own pursuit of financial independence. Or your impending lifetime of occupational drudgery.

Oh, wait, that’s a good point: occupational drudgery. What if you haven’t found a job you love? What if you have other things you’d rather do while you’re younger and more mobile? What if you live a simple lifestyle by choice and already feel as if you have way more than you need? What if you already have your own answers to the questions about kids and college and mortgages and savings? What if your occupation interferes with everything else in your life?

Would these writers be so gloomy if they were financially independent? That’s the real issue, isn’t it: being unsure whether their income or savings will sustain their quality of life for the rest of their lives. What if they had a military pension and cheap healthcare? Even without the military pension, what if they’d saved enough from the military and a bridge career that they could annuitize their own retirement income and pay for their own health insurance?

When we started working, we were all in search of “doing what you love”. If you find your dream career then you should work as long as you enjoy it. However, at some point your priorities may change. You may decide that family or travel are more important to you than your occupation. There may be too many conflicts between your occupation and the rest of your life, and your employer can’t be flexible enough for you to reconcile the issues. You may develop other interests. Even if you still manage to balance your priorities, your work may change and no longer be as fulfilling as you used to find it.

When the fun stops, you can always find other work. But when you reach one of those decision points, then maybe– just maybe— it’s easier to handle the transition if you’re financially independent. Maybe, when you need to make a change, it’s good to have the resources to live without a paycheck for a while as you resolve the situation and decide on your next step.

When you’re working for a paycheck, maybe you shouldn’t worry about running out of money in retirement. Maybe you should worry about not having work that you enjoy. After a few years of work-related stress, suddenly Medicare’s health won’t seem like such a big issue anymore. Suddenly a few percentage points of uncertainties of retirement planning won’t seem like such an obstacle. When you reach financial independence, you could start making your own choices about the work you enjoy doing. You don’t need to have a plan for every day of the rest of your life– you just need to be able to make your own choices.

30 years ago, an entire generation was blissfully unaware of the financial risks of retirement. Even 10 years ago we didn’t have good answers to the last few percentage points of uncertainty. Today, however, retirement calculators and annuitized income and variable spending plans have whittled away at that uncertainty. The biggest retirement challenge may be figuring out how you want to spend your time, not your money.

It’s all about priorities, and financial independence gives you the chance to set your own priorities. If you enjoy working then that’s what you should do. If your personal identity is tied to your occupation then you should keep working until you’re ready for a different life and a different identity. If you’d rather stop working at an earlier age, then you’ll figure out ways to handle the issues raised by these writers. (Other early retirees have solved the same problems, and you’ll find a solution that works for you.) But more importantly, once you’ve aligned your priorities with your values then you’ll feel more fulfilled and satisfied by the actions you’re taking to get there. And when you reach financial independence then you’ll have the flexibility to make the really tough decisions about what you want to do with the rest of your life.

There are still times when I’m so busy that I wonder whether I’m really retired. Some weeks it’d be easier to sit on my butt in the workplace and let someone else tell me what I’m going to do all day. But maybe I’m lucky: I have a military certificate that assures me I’m really retired. And when the surf is up, I can go.

You’ll have to decide for yourself where to draw the line between working for income and pursuing your interests. Financial independence will give you the flexibility and the time to make your own choices.

You also have to be responsible for your own entertainment.

By the way, Robert Brokamp: if you really, truly, deep-down believe that retirees sit on their butts all day, then you lack imagination. I hope you’ve learned enough about retirement from the people you’ve interviewed to figure out how you’d like to enjoy your own retirement.

WHAT I DO: I help you reach financial independence. For free. I retired in 2002 after 20 years in the Navy's submarine force. I wrote "The Military Guide to Financial Independence and Retirement" to share the stories of over 50 other financially independent servicemembers, veterans, and families. All of my writing revenue is donated to military-friendly charities.